The Informant
by Mokulule
Summary: Jiraya gains an informant inside an organization that will rise to great infamy in the coming years.


**The Informant**

The toad sage watched the swaying hips appreciatively, as the dark haired woman sauntered to the bar ignoring several advances from the patrons. Her dark eyes had singled him out immediately upon entering and so Jiraya had first come to the conclusion that the lovely lady was an assassin - and a good one as her eyes had only lingered on him very briefly during her scan of the bar.

Not a man to beat around the bush he'd left his own place to squeeze himself in between her and an overeager suitor. A small bit of leaked killer intent made the man back off easily. Turning back to the dark beauty he realized that he'd been wrong in his assumption. That girl was not an assassin merely a pawn.

She tilted her head and smiled seductively at him.

"How about we take this somewhere else?"

He grinned like he usually did and swiped his arm out generously indicating she lead the way.

"After you." The gallant Jiraya was not one to say no to a woman, even if there was a trap involved. He would rather face it head on.

Many jealous looks was directed his way and the irony made his grin wider. If they knew the truth of the situation, maybe they wouldn't be so envious.

Oo o oO

"Why don't you come out? I know you are there, really to think I would be cheated by a genjutsu cast on a girl," he drawled nonchalantly and added almost sourly, "that is grossly underestimating my abilities."

"Do you really think you would have detected the genjutsu, if I hadn't wanted you to?"

Jiraya barely held back his shock. The person who stepped into the light was just a dark haired boy of no more than 14. His identity however was quickly revealed when their eyes met; sharingan. Quickly he averted his eyes from direct eye contact and focused instead on the kid's chin. Just six months prior the sharingan had increased massively in rarity and there was only one person this could be: Uchiha Itachi.

The sannin had to reevaluate his statement. If the Uchiha really didn't want him to discover the genjutsu would he have succeeded? Frankly he didn't know. He only knew off Itachi, he'd never actually met him before. What he knew however was quite troubling. Hailed as a prodigy even within the genius clan itself. A clan that was now left with only two members, because of that same prodigy.

He had no choice but to keep talking and hope to glean some information and maybe figure out his intentions.

"You did not have the guts to walk up to me yourself?" He was half hoping to rile the pale boy, but he wasn't really surprised when the youth just replied calmly - one didn't become ANBU without impressive control over one's emotions.

"I thought it would seem less suspicious if it were a woman seeking you out. Your reputation is spread wide and far after all." He seemed to pause thoughtfully for a moment, "though I guess, if I made a small effort, I could pass for a woman."

It was true. The young Uchiha was tall for his age but was still essentially 'just a boy' so his body wasn't as angular and his shoulders not as broad as they would become within a few years, and even then Uchihas were slender to begin with. Not to mention the long eye lashes and hair. Jiraya grimaced.

"That is just disturbing."

Itachi quirked his lips amusedly obviously expecting the reaction.

"I'm quite glad you agree on that actually, but maybe we should get to business?"

This was it then Jiraya thought. Testing himself on the clan hadn't been enough he had to... as if reading his mind the boy interrupted him.

"I have no intention of finding out who's stronger between the legendary Jiraya and the infamous Uchiha Itachi."

The Sannin's mouth dropped open in confusion.

"Then what the hell do you want?"

Jiraya was not scared of the kid, if it came to a fight he would fight him head on even if a genjutsu master wasn't the best matchup for him. He was certain he had a few aces up his sleeves the Uchiha didn't know of. But if the teen wasn't here to fight, Jiraya was royally perplexed.

"I," the youth hesitated and for the briefest moment there was a crack in the impassive facade; pain and lot's of it was behind it. A thought niggled at the back of his mind. He took a step forward and the boy took one backwards only to find his back against the wall of the alley. It clicked into place and the puzzle created a most horrific picture.

"Who ordered you boy?" It was the logical conclusion, but it made his blood run cold; he'd much rather believe the genuis in front of him had gone insane from the pressure.

"Danzo, the council, the Sandaime," he answered the question monotonously, but Jiraya knew now that it was not a sign of having no emotion, rather it was because the emotions were too painful to acknowledge.

The teen took a threatening step forward as his red eyes narrowed.

"You will not tell anyone about this."

The Sannin nodded with a newfound respect for the Uchiha, the boy was an exceptional shinobi. It was an abominable situation and he would ask his old teacher about the details the next time he swung by Konoha (he could not believe Sarutobi had sanctioned such a thing without good reason), but the kid would not accept his pity.

"I have joined an organization by name of Akatsuki, you lost interest in it when Orochimaru left, but I know they are planning something."

"So you are offering me?"

"Information."

"In return for?" Jiraya already knew the answer, but couldn't help asking.

"You will warn Konoha."

"Nothing for yourself?" he baited and sharingan eyes narrowed in insult.

"I am a Konoha shinobi."

The scratch through the symbol on his hitai ate said otherwise and Jiraya could only guess at how much it had hurt to etch it there.

**Author's Note:**

Just a little something I had lying around and decided to touch up on. I consider adding future meetings between them up until the point where they both die, if I do so it will be like a series of short oneshots added as chapters. Thank you for reading^^


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